journal article·2014-01-29

Hydrophobization and characterization of internally crosslink-reinforced cellulose fibers

Zohreh Sabzalian, Md Nur Alam, Theo G. M. van de Ven

Publisher page

Abstract

Transforming hydrophilic cellulose fibers into hydrophobic, non-hygroscopic fibers could potentially lead to a variety of new products, such as flexible packaging, self-cleaning films and strength-enhancing agents in polymer composites. To achieve this, softwood cellulose pulp was chemically modified with successive chemical treatments. First the C2 and C3 hydroxyl groups of the glucose units were selectively oxidized by periodate oxidation to reactive dialdehyde units on the cellulose chain, followed by a Schiff base reaction with 1,12-diaminododecane to crosslink the microfibrils within the fiber wall. This was done, because introducing high levels of alkylation resulted in fiber disintegration, which could be prevented by crosslinking. After internal crosslinking a second Schiff base reaction was performed with butylamine. This procedure yielded highly hydrophobic and low-hygroscopic cellulosic materials. The modified cellulose fibers were investigated by a variety of techniques, including Fourier transform infrared spectroscopy, nuclear magnetic resonance, field-emission scanning electron microscopy, thermogravimetric analysis, X-ray diffraction, moisture sorption and water contact angle measurements. The water uptake of the fibers after being modified reduced from 4 to around 1 %. Various reaction conditions were studied for optimum performance.
Source: openaire · Quality: candidate unverified · Source record ↗

Research context

OpenAlex topics: Advanced Cellulose Research Studies · Natural Fiber Reinforced Composites · Electrospun Nanofibers in Biomedical Applications

SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.

References (35)

Show source-provided references
1. Alam MN, Antal M, Tejado A, van de Ven TGM (2012) Salt-induced acceleration of chemical reactions in cellulose nanopores. Cellulose 19(2):517–52210.1007/s10570-011-9649-1 ↗
2. Balu B, Breedveld V, Hess DW (2008) Fabrication of ‘‘roll-off’’ and ‘‘sticky’’ superhydrophobic cellulose surfaces via plasma processing. Langmuir 24(9):4785–479010.1021/la703766c ↗
3. Bledzki AK, Reihmane S, Gassan J (1998) Thermoplastics reinforced with wood fillers: a literature review. Polym Plast Technol Eng 37(4):451–46810.1080/03602559808001373 ↗
4. Casu B, Naggi A, Torri G, Allegra G, Meille SV, Cosani A, Terbojevich M (1985) Stereoregular acyclic polyalcohols and polyacetates from cellulose and amylase. Macromolecules 18:2762–276710.1021/ma00154a068 ↗
5. Cunha AG, Freire CSR, Silvestre AJD, Neto CP, Gandini A, Orblin E, Fardim P (2007) Highly hydrophobic bio-polymers prepared by the surface pentafluorobenzoylation of cellulose substrates. Biomacromolecules 8(4):1347–135210.1021/bm0700136 ↗
6. Davidson GF, Nevell TP (1955) The oxidation of the aldehyde groups in periodate oxycelluloses by chlorous acid. J Text Inst 46:T40710.1080/19447027.1955.10750329 ↗
7. Duchemin B, Newman R, Staiger M (2007) Phase transformations in microcrystalline cellulose due to partial dissolution. Cellulose 14:311–32010.1007/s10570-007-9121-4 ↗
8. Gandini A, Belgacem MN (2008) The state of the art. In: Belgacem MN, Gandini A (eds) Monomers, polymers and composites from renewable resources, 1st edn. Elsevier, Amsterdam, pp 1–1610.1016/B978-0-08-045316-3.00001-6 ↗
9. Goetz L, Mathew A, Oksman K, Gatenholm P, Ragauskas A (2009) A novel nanocomposite film prepared from crosslinked cellulosic whiskers. Carbohydr Polym 75:85–8910.1016/j.carbpol.2008.06.017 ↗
10. Han S, Lee M, Kim BK (2010) Crosslinking reactions of oxidized cellulose fiber. I. Reactions between dialdehyde cellulose and multifunctional amines on lyocell fabric. J Appl Polym Sci 117:682–69010.1002/app.30895 ↗
11. Hofreiter BT, Wolff IA, Mehltretter L (1957) Chlorous acid oxidation of periodate oxidized cornstarch. J Am Chem Soc 79:6457–646010.1021/ja01581a026 ↗
12. Hou QX, Liu W, Liu ZH, Bai LL (2007) Characteristics of wood cellulose fibers treated with periodate and bisulfite. Ind Eng Chem Res 46:7830–783710.1021/ie0704750 ↗
13. Howsman JA (1949) Water sorption and the poly-phase structure of cellulose fibers. Text Res J 19:152–16210.1177/004051754901900303 ↗
14. Isogai A, Usuda M, Kato T, Uryu T, Atalla RH (1989) Solid-state CP/MAS carbon-13 NMR study of cellulose polymorphs. Macromolecules 22:3168–317210.1021/ma00197a045 ↗
15. Keshk SMAS (2008) Homogenous reactions of cellulose from different natural sources. Carbohydr Polym 74:94210.1016/j.carbpol.2008.05.022 ↗
16. Kim UJ, Shigenori K (2001) Thermal decomposition of dialdehyde cellulose and its nitrogen-containing derivatives. Thermochim Acta 369:79–8510.1016/S0040-6031(00)00734-6 ↗
17. Kim UJ, Kuga S, Wada M, Okano T, Kondo T (2000) Periodate oxidation of crystalline cellulose. Biomacromolecules 1:488–49210.1021/bm0000337 ↗
18. Liimatainen H, Visanko M, Sirviö JA, Osmo EO, Hormi NJ (2012) Enhancement of the nanofibrillation of wood cellulose through sequential periodate–chlorite oxidation. Biomacromolecules 13:1592–159710.1021/bm300319m ↗
19. Maekawa E, Koshijima T (1984) Properties of 2,3-dicarboxy cellulose combined with various metallic ions. J Appl Polym Sci 29:2289–229710.1002/app.1984.070290705 ↗
20. Maekawa E, Koshijima T (1991) Preparation and structural consideration of nitrogen-containing derivatives obtained from dialdehyde celluloses. J Appl Polym Sci 42:169–17810.1002/app.1991.070420120 ↗
21. Maekawa E, Kosaki T, Koshijima T (1986) Periodate oxidation of mercerized cellulose and regenerated cellulose. Wood Res 73:44–49
22. Nevell TP (1963) In: Whistler RL (ed) Methods in carbohydrate chemistry, vol III. Academic Press, New York, p 164
23. Nishiyama Y, Langan P, Chanzy H (2002) Crystal structure and hydrogen-bonding system in cellulose Iâ from synchrotron X-ray and neutron fiber diffraction. J Am Chem Soc 124:9074–908210.1021/ja0257319 ↗
24. Rutherford HA, Minor FW, Martin AR, Harris M (1942) Oxidation of cellulose: the reaction of cellulose with periodic acid. J Res Nat Bur Stand 29:13110.6028/jres.029.004 ↗
25. Segal L, Creely JJ, Martin AE, Conrad CM (1959) An empirical method for estimating the degree of crystallinity of native cellulose using the X-ray diffractometer. Text Res J 29:78610.1177/004051755902901003 ↗
26. Sirviö J, Hyvakkö U, Liimatainen H, NiinimakI J, Hormi O (2011) Periodate oxidation of cellulose at elevated temperatures using metal salts as cellulose activators. Carbohydr Polym 83:1293–129710.1016/j.carbpol.2010.09.036 ↗
27. Spedding H (1960) Infrared spectra of periodate–oxidised cellulose. J Chem Soc 73:3147–315210.1039/jr9600003147 ↗
28. Symons MCR (1955) Evidence for formation of free-radical intermediates in some reactions involving periodate. J Chem Soc :2794–279610.1039/jr9550002794 ↗
29. Tejado A, Alam MN, Antal M, Yang H, van de Ven TGM (2012) Energy requirements for the disintegration of cellulose fibers into cellulose nanofibers. Cellulose 19:831–84210.1007/s10570-012-9694-4 ↗
30. Varma AJ, Chavan VB (1995) Thermal properties of oxidized cellulose. Cellulose 2:41–4910.1007/BF00812771 ↗
31. Varma AJ, Chavan VB, Rajmohanan PR, Ganapathy S (1997) Some observations on the high-resolution solid-state CP–MAS C13-NMR spectra of periodate–oxidised cellulose. Polym Degrad Stab 58(3):257–26010.1016/S0141-3910(97)00049-9 ↗
32. von Wangelin AJ, Neumann H, Gordes D, Klaus S, Strubing D, Beller M (2003) Multicomponent coupling reactions for organic synthesis: chemoselective reactions with amide–aldehyde mixtures. Chem Eur J 9:4286–429410.1002/chem.200305048 ↗
33. Wu M, Kuga S (2006) Cationization of cellulose fabrics by polyallylamine. J Appl Polym Sci 100(2):1668–167210.1002/app.22895 ↗
34. Yang H, Alam MN, van de Ven TGM (2013) Highly charged nanocrystalline cellulose and dicarboxylated cellulose from periodate and chlorite oxidized cellulose fibers. Cellulose 20:1865–187510.1007/s10570-013-9966-7 ↗
35. Yuen SN, Choi SM, Phillips DL, Ma CY (2009) Raman and FTIR spectroscopic study of carboxymethylated non-starch polysaccharides. Food Chem 114:1091–109810.1016/j.foodchem.2008.10.053 ↗